Pieter Calitz defeated Andrej Kracman 6-2 6-3 in the South Africa Masters 1 semi-final on hard. The upset overturned the form book — Andrej Kracman came in leading the head-to-head 1–0. Pieter Calitz claimed a first win over Andrej Kracman in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-10-16 | South Africa Masters 2 | R16 | hard | Andrej Kracman | 6-4 6-7 6-1 |